Chestertown Beach Hotels
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If You Are in a Hurry
Here’s a quick list of the best hotels in Chestertown





Nestled along Maryland's picturesque Eastern Shore, Chestertown offers a unique blend of coastal charm and historical allure, making it an ideal destination for beach lovers seeking a serene getaway. With stunning waterfront views and delightful accommodations that cater to every budget, the town boasts a selection of hotels by the beach that promise not only comfort but also easy access to sandy shores and vibrant local culture. Whether you're looking for a cozy retreat or an upscale experience, exploring these beachfront havens will ensure your stay is both memorable and rejuvenating.
Best Hotels on the Beach in Chestertown
Eastern Shore Getaway Walk to Tolchester Marina!

Eastern Shore Getaway Walk to Tolchester Marina! is a charming holiday home located in Rock Hall, featuring air-conditioned accommodations with a balcony and complimentary WiFi. It offers spacious lodging with five bedrooms, a flat-screen TV with cable channels, and a fully equipped kitchen complete with essential appliances. Guests can enjoy the convenience of on-site parking and free bicycle rentals to explore the picturesque surroundings. The property also boasts a cozy fireplace and an on-site bar. - Spacious 5-bedroom layout - Free WiFi and parking available - Fully equipped kitchen for meal preparation - Free use of bicycles for local exploration - Close proximity to Tolchester Marina
Waterfront Millington Vacation Rental with Hot Tub!

Waterfront Millington Vacation Rental with Hot Tub! is a spacious holiday home located in Millington, just 39 km from Snowland and 40 km from the Delaware State Police Museum and Education Center. The property boasts air conditioning, free WiFi, and features seven bedrooms along with a fully equipped kitchen that includes a dishwasher and an oven. Guests can enjoy the comfort of provided towels and bed linen, as well as the warmth of a fireplace. Nearby attractions include Air Mobility Command Museum (40 km) and Dover International Speedway (42 km), while New Castle Airport is situated 63 km away. - Spacious accommodation with seven bedrooms - Fully equipped kitchen for convenient meal preparation - Relaxing hot tub on-site - Free WiFi available throughout the property - Close proximity to local attractions
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office

Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office is located in Chestertown and features a variety of amenities including water sports facilities, complimentary bicycles, and a bar. The property boasts access to a patio, a pool table, free private parking, and free WiFi. This spacious holiday home includes 5 bedrooms, a flat-screen TV with streaming services, and a fully equipped kitchen with modern appliances such as a dishwasher and microwave. Guests can enjoy meals at the family-friendly restaurant serving American cuisine for lunch and dinner or relax in the picnic area. The nearest airport is New Castle Airport, situated 91 km away. - Proximity to the beach - Family-friendly atmosphere - Fully equipped kitchen - On-site dining options - Ample recreational facilities
Family-Friendly Cottage, Walk to the Beach!

Family-Friendly Cottage, Walk to the Beach! offers comfortable accommodation in Kennedyville with features such as free bikes and complimentary WiFi throughout the property. This holiday home includes 2 bedrooms, a flat-screen TV, and a fully equipped kitchen with modern appliances like a dishwasher, oven, washing machine, microwave, and toaster. Guests can enjoy cozy evenings by the fireplace in this welcoming space. The nearest airport is New Castle Airport, located 63 km away. - Family-friendly environment - Proximity to the beach - Fully equipped kitchen - Free bikes available for guests - Cozy fireplace for relaxation
Carriage House Hideaway In Center of Chestertown

Carriage House Hideaway is located in the heart of Chestertown, Maryland, offering a serene garden setting for guests to enjoy. This non-smoking accommodation provides a comfortable retreat with easy access to local attractions. The nearest airport is New Castle Airport, situated 77 km away. - Central location in Chestertown - Scenic garden setting - Non-smoking environment - Proximity to local attractions - Peaceful and relaxing atmosphere
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown is conveniently located less than 1 mile from Washington College, offering free Wi-Fi throughout the property. Each room features a flat-screen TV, microwave, and refrigerator, all adorned with soft colors and dark wood furnishings. Guests can enjoy a hot continental breakfast daily and have access to an on-site fitness center and business center, along with laundry facilities. The scenic Chester River, ideal for kayaking or canoeing, is just 2 miles away, while the vibrant Chestertown center filled with boutique shops and restaurants is merely a 5-minute drive. - Close proximity to Washington College - Complimentary hot continental breakfast - On-site fitness and business centers - Laundry facilities available - Access to outdoor activities near Chester River
Driftwood Inn

Located just a 6-minute walk from Washington College, the Driftwood Inn offers comfortable accommodations with rustic wood paneling and soft neutral colors. Guests can enjoy free Wi-Fi and a 24-hour front desk service, while all rooms are equipped with cable TV featuring HBO channels, microwaves, and refrigerators. The motel provides complimentary coffee in the lobby along with vending machines for drinks. Additional services such as copy and fax are available at the front desk. Nearby attractions include Downtown Chestertown, 2 miles away, Chester River Yacht and Country Club at 2.5 miles, and Remington Farms National Wildlife Preserve located a short 14-minute drive from the property. - Convenient location near Washington College - Free Wi-Fi throughout the property - Comfortable rooms with essential amenities - Access to local attractions within a short distance - 24-hour front desk for guest assistance